bis-noryangonin | 13709-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis-noryangonin
• 英文别名: Bisnoryangonin；4-hydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]pyran-2-one
• CAS: 13709-27-8
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: ORVQWHLMVLOZPX-ZZXKWVIFSA-N

物化性质

• 熔点：
  200-205 °C
• 沸点：
  440.3±45.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基-6-甲基-2H-吡喃酮 在 三溴化硼 、 sodium hydride 、 magnesium 、 乙硫醇 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.42h， 生成 bis-noryangonin
  参考文献：
  名称：

  真菌生物发光的化学基础

  摘要：

  许多种类的真菌自然产生光，这种现象称为生物发光，但是，尚未报道用于产生光的化学反应中使用的真菌底物。我们确定了真菌化合物萤光素3-羟基hispidin，它是通过前体hispidin（一种已知的真菌和植物次生代谢物）的氧化而生物合成的。真菌萤光素与其他八种已知萤光素没有结构相似性。此外，结果表明3-羟基hispidin导致发光真菌的四个不同属的提取物中的生物发光，从而暗示了真菌生物发光的常见生化机制。

  DOI：

  10.1002/anie.201501779

文献信息

• Reshaping the 2‐Pyrone Synthase Active Site for Chemoselective Biosynthesis of Polyketides
  作者：Yu Zhou、Evan N. Mirts、Sangdo Yook、Matthew Waugh、Rachel Martini、Yong‐Su Jin、Yi Lu

  DOI：10.1002/anie.202212440

  日期：2023.1.26

  Implementation of novel synthetic pathways into metabolic network is challenging. Empowered by protein engineering and synthetic biology, a whole-cell transformation process is reported to utilize engineered 2-pyrone synthase with novel reactivity in metabolic networks to convert carboxylic acids and intracellular malonyl-CoA directly into the pyrone products with high yields, catalytic efficiency and good selectivity

  将新的合成途径实施到代谢网络中具有挑战性。据报道，在蛋白质工程和合成生物学的支持下，全细胞转化过程利用在代谢网络中具有新颖反应性的工程化 2-吡喃酮合酶，将羧酸和细胞内丙二酰辅酶 A 直接转化为吡喃酮产品，具有高产率、催化效率和良好的选择性。
• ENZYMES OF LUCIFERIN BIOSYNTHESIS AND USE THEREOF
  申请人：Light Bio, Inc

  公开号：EP3816282A1

  公开（公告）日：2021-05-05

  Present invention is aimed at identification of new fungal luciferin biosynthesis enzymes, nucleic acids able to encode these enzymes, and proteins able to catalyze certain stages of the fungal luciferin biosynthesis. The invention also provides for application of nucleic acids for producing said enzymes in a cell or organism. Methods for in vitro or in vivo preparation of chemical compounds identical to fungal luciferins and preluciferins are also provided. Vectors comprising nucleic acid described in the present invention are also provided. In addition, the present invention provides expression cassettes comprising the nucleic acid of the present invention and regulatory elements necessary for nucleic acid expression in a selected host cell. Besides, cells, stable cell lines, transgenic organisms (e.g. plants, animals, fungi, or microorganisms) including nucleic acids, vectors, or expression cassettes of the present invention are also provided. Present invention also provides combinations of nucleic acids to obtain autonomously luminous cells, cell lines, or transgenic organisms. In preferred embodiments, cells or transgenic organisms are capable to produce fungal luciferin from precursors. In some embodiments, cells or transgenic organisms are capable to produce fungal preluciferin from precursors. In some embodiments, cells or transgenic organisms are capable of bioluminescence in the presence of a fungal luciferin precursor. In some embodiments, cells or transgenic organisms are capable of autonomous bioluminescence. Combinations of proteins for producing luciferin or its precursors from more simple chemical compounds are also provided. A kit containing nucleic acids, vectors, or expression cassettes of the present invention for producing luminous cells, cell lines, or transgenic organisms is also provided.

  本发明旨在鉴定新的真菌荧光素生物合成酶、能够编码这些酶的核酸以及能够催化真菌荧光素生物合成某些阶段的蛋白质。本发明还提供了核酸在细胞或生物体内产生上述酶的应用。本发明还提供了体外或体内制备与真菌荧光素和预荧光素相同的化合物的方法。还提供了包含本发明所述核酸的载体。此外，本发明还提供了包含本发明核酸和在所选宿主细胞中表达核酸所需的调控元件的表达盒。此外，本发明还提供了包括本发明核酸、载体或表达盒的细胞、稳定细胞系、转基因生物（如植物、动物、真菌或微生物）。本发明还提供了核酸组合，以获得自主发光的细胞、细胞系或转基因生物。在优选的实施方案中，细胞或转基因生物能够从前体产生真菌荧光素。在某些实施方案中，细胞或转基因生物能够从前体产生真菌前荧光素。在某些实施方案中，细胞或转基因生物能够在真菌荧光素前体存在的情况下发出生物荧光。在某些实施方案中，细胞或转基因生物能够自主发出生物荧光。此外，还提供了从更简单的化合物中生产荧光素或其前体的蛋白质组合。还提供了含有本发明核酸、载体或表达盒的试剂盒，用于生产发光细胞、细胞系或转基因生物。
• In Vitro Precursor-Directed Synthesis of Polyketide Analogues with Coenzyme A Regeneration for the Development of Antiangiogenic Agents
  作者：Moon Il Kim、Seok Joon Kwon、Jonathan S. Dordick

  DOI：10.1021/ol901243e

  日期：2009.9.3

  Polyketide analogues are produced via in vitro reconstruction of a precursor-directed polyketide biosynthetic pathway. Malonyl-CoA synthetase (MCS) was used in conjunction with chalcone synthase (CHS), thereby allowing efficient use of synthetic starter molecules and malonate as extender. Coenzyme-A was recycled up to 50 times. The use of a simple immobilization procedure resulted in up to a 30-fold higher yield of pyrone CHS products than that obtained with the free enzyme solutions.
• Pyrone polyketides synthesized by a type III polyketide synthase from Drosophyllum lusitanicum
  作者：Aphacha Jindaprasert、Karin Springob、Jürgen Schmidt、Wanchai De-Eknamkul、Toni M. Kutchan

  DOI：10.1016/j.phytochem.2008.03.013

  日期：2008.12

  To isolate cDNAs involved in the biosynthesis of acetate-derived naphthoquinones in Drosophyllum lusitanicum, an expressed sequence tag analysis was performed. RNA from callus cultures was used to create a cDNA library from which 2004 expressed sequence tags were generated. One cDNA with similarity to known type III polyketicle synthases was isolated as full-length sequence and termed DluHKS. The translated polypepticle sequence of DIuHKS showed 51-67% identity with other plant type III PKSs. Recombinant DIuHKS expressed in Escherichia coli accepted acetyl-coenzyme A (CoA) as starter and carried out sequential decarboxylative condensations with malonyl-CoA yielding ot-pyrones from three to six acetate units. However, naphthalenes, the expected products, were not isolated. Since the main compound produced by DIuHKS is a hexaketicle ot-pyrone, and the naphthoquinones in D. lusitanicum are composed of six acetate units, we propose that the enzyme provides the backbone of these secondary metabolites. An involvement of accessory proteins in this biosynthetic pathway is discussed. (c) 2008 Elsevier Ltd. All rights reserved.
• ENZYMATIC SYNTHESIS OF KAVALACTONES AND FLAVOKAVAINS
  申请人：Whitehead Institute for Biomedical Research

  公开号：US20190271015A1

  公开（公告）日：2019-09-05

  Disclosed are methods, compositions, proteins, nucleic acids, cells, vectors, compounds, reagents, and systems for the preparation of kavalactones, flavokavains, and kavalactone and flavokavain biosynthetic intermediates using enzymes expressed in heterologous host cells, such as microorganisms or plants, or using in vitro enzymatic reactions. This invention also provides for the expression of the enzymes by recombinant cell lines and vectors. Furthermore, the enzymes can be components of constructs such as fusion proteins. The kavalactones produced can be utilized to treat anxiety disorder, insomnia, and other psychological and neurological disorders. The flavokavains produced can be utilized to treat various cancers including colon, bladder, and breast cancers.